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Category:Phenethylamine

Revision as of 02:31, 18 August 2014 by >PJosepherum
Substitutive structure of a phenethylamine molecule.

Substituted phenethylamine refers to a class of compounds which typically produce strong psychedelic effects.

Chemistry

Phenethylamine comprises a benzene ring attached to a mono-amine group via an ethyl side-chain. Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, efficacy and half-life.

Phenethylamines, tabulated by structure
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name Biologic activity
meta-Tyramine OH 3-hydroxyphenethylamine Trace amine
para-Tyramine OH 4-hydroxyphenethylamine Trace amine
Dopamine OH OH 3,4-dihydroxyphenethylamine Catecholamine neurotransmitter
Epinephrine (Adrenaline) CH3 OH OH OH β,3,4-trihydroxy-N-methylphenethylamine Catecholamine neurotransmitter/Fight or Flight hormone
Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine Catecholamine neurotransmitter/Fight or Flight hormone
meta-Octopamine OH OH β,3-dihydroxyphenethylamine Trace amine
para-Octopamine OH OH β,4-dihydroxyphenethylamine Trace aminergic α-adrenoceptor agonist
Phenylephrine CH3 OH OH β,3-dihydroxy-N-methylphenethylamin α-adrenergic agonist; decongestant
6-Hydroxydopamine OH OH OH 2,4,5-trihydroxyphenethylamine neurotoxic agent for the dopamine and norepinephrine receptors
Salbutamol C(CH3)3 OH OH CH2OH β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine Short-action β2-adrenergic agonist
β-Methylphenethylamine CH3 β-methylphenethylamine Stimulant
Amphetamine CH3 α-methylphenethylamine Monoamine releasing agent; Stimulant
N-Methylphenethylamine CH3 N-methylphenethylamine Endogenous amphetamine isomer; Trace amine
Methamphetamine CH3 CH3 N-methylamphetamine Monoamine releasing agent; Stimulant; dopaminergic neurotoxin
Methylphenidate -CH2-CH2-CH2-CH2- C(OCH3)=O N,α-butylene-β-methoxycarbonylphenethylamine NDRI; Stimulant
Ephedrine / Pseudoephedrine CH3 CH3 OH N-methyl-β-hydroxyamphetamine Releasing agent; stimulant; decongestant
Cathine CH3 OH d-β-hydroxyamphetamine Somewhat selective norepinephrine releasing agent
Cathinone CH3 =O β-ketoamphetamine Selective norepinephrine and dopamine releasing agent
Methcathinone CH3 CH3 =O N-methylcathinone Selective norepinephrine and dopamine releasing agent
Mephedrone CH3 CH3 =O CH3 4-methylmethcathinone Stimulant, unknown pharmacodynamics actions
Ethcathinone CH2CH3 CH3 =O N-ethylcathinone Stimulant and Norepinephrine releasing agent
Bupropion C(CH3)3 CH3 =O Cl 3-chloro-N-tert-butyl-β-ketoamphetamine NDRI
Norfenfluramine CH3 CF3 3-trifluoromethyl-amphetamine SSRA
Fenfluramine CH2CH3 CH3 CF3 3-trifluoromethyl-N-ethyl-amphetamine SSRA
Phentermine 2CH3 α,α-dimethylphenethylamine Stimulant, anorectic
5-APB CH3 -CH=CH-O- 5-(2-aminopropyl)benzofuran stimulant, entactogen
6-APB CH3 -O-CH=CH- 6-(2-aminopropyl)benzofuran stimulant, entactogen
MDA CH3 -O-CH2-O- 3,4-methylenedioxyamphetamine Stimulant, psychedelic, entactogen
MDEA CH2CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-ethylamphetamine psychedelic, entactogen and releasing agent
MDMA CH3 CH3 -O-CH2-O- 3,4-methylenedioxy-N-methylamphetamine psychedelic, entactogen and releasing agent
MDMC CH3 CH3 =O -O-CH2-O- 3,4-methylenedioxymethcathinone psychedelic, entactogen and releasing agent
Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine Serotonergic Psychedelic
Proscaline OCH3 OCH2CH2CH3 OCH3 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine Stimulant, entactogen and euphoriant
Metaescaline OCH2CH3 OCH3 OCH3 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine Serotonergic Psychedelic, stimulant, entactogen and euphoriant
Allylescaline OCH3 OCH2CH1CH2 OCH3 4-Allyloxy-3,5-dimethyloxyphenylethylamine Stimulant, entactogen and euphoriant
Asymbescaline OCH2CH3 OCH2CH3 OCH3 3,4-Diethoxy-5-methoxyphenethylamine Psychedelic and euphoriant
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine psychedelic
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine Psychedelic
DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine Psychedelic
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine Stimulant
DOC CH3 OCH3 Cl OCH3 2,5-dimethoxy-4-chloroamphetamine Psychedelic
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine Psychedelic, stimulant, entactogen and euphoriant
βk-2C-B =O OCH3 Br OCH3 2,5-dimethoxy-4-bromo-β-ketophenethylamine Psychedelic, stimulant, entactogen and euphoriant
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine Psychedelic
2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodophenethylamine Psychedelic, stimulant
2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methylphenethylamine Psychedelic, stimulant
2C-E OCH3 CH2-CH3 OCH3 2,5-dimethoxy-4-ethylphenethylamine Psychedelic
2C-P OCH3 CH2-CH3-CH3 OCH3 2,5-dimethoxy-4-propylphenethylamine Entactogen, euphoriant and Psychedelic
2C-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine None
2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine euphoriant
2C-T-2 OCH3 S-CH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine Psychedelic
2C-T-4 OCH3 S-CH(CH3)2 OCH3 2,5-dimethoxy-4-isopropylthio-phenethylamine Psychedelic
2C-T-7 OCH3 S-CH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine Psychedelic
2C-T-8 OCH3 S-CH2-C3H5 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine Psychedelic
2C-T-9 OCH3 S-C(CH3)3 OCH3 2,5-dimethoxy-4-tert-butylthio-phenethylamine Psychedelic
2C-T-21 OCH3 S-CH2-CH2-F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine Psychedelic and euphoriant
25B-NBOMe CH2-C6H4-OCH3 OCH3 Br OCH3 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25C-NBOMe CH2-C6H4-OCH3 OCH3 Cl OCH3 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25I-NBOMe CH2-C6H4-OCH3 OCH3 I OCH3 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25D-NBOMe CH2-C6H4-OCH3 OCH3 CH2 OCH3 2-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25E-NBOMe CH2-C6H4-OCH3 OCH3 CH2-CH3 OCH3 2-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25P-NBOMe CH2-C6H4-OCH3 OCH3 CH2-CH3-CH3 OCH3 2-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25F-NBOMe CH2-C6H4-OCH3 OCH3 F OCH3 2-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
Mescaline-NBOMe CH2-C6H4-OCH3 OCH3 OCH3 OCH3 N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine Psychedelic
25I-NBOH CH2–C6H4–OH OCH3 I OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
25C-NBOH CH2–C6H4–OH OCH3 Cl OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine Psychedelic
25B-NBOH CH2–C6H4–OH OCH3 Br OCH3 N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine Psychedelic
25I-NBF CH2–C6H4–F OCH3 I OCH3 N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
Short Name RN Rα Rβ R2 R3 R4 R5 Full Name

Pharmacology

Phenethylamines are believed to produce their psychedelic effect primarily by partial agonism of 5-HT2A receptors.

Several neurotransmitters are derived from phenethylamine, such as:

References

wikipedia:Tryptamine

Subcategories

This category has the following 6 subcategories, out of 6 total.

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